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Chemical Structure| 3199-50-6 Chemical Structure| 3199-50-6

Structure of 3199-50-6

Chemical Structure| 3199-50-6

1-(5-Bromofuran-2-yl)ethanone

CAS No.: 3199-50-6

4.5 *For Research Use Only !

Cat. No.: A306578 Purity: 95%

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Product Details of [ 3199-50-6 ]

CAS No. :3199-50-6
Formula : C6H5BrO2
M.W : 189.01
SMILES Code : CC(=O)C1=CC=C(Br)O1
MDL No. :MFCD06657513
InChI Key :CASNGOWLOZSVMA-UHFFFAOYSA-N
Pubchem ID :11030585

Safety of [ 3199-50-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P302+P352-P305+P351+P338

Application In Synthesis of [ 3199-50-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3199-50-6 ]

[ 3199-50-6 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 186581-53-3 ]
  • [ 1899-24-7 ]
  • [ 3199-50-6 ]
  • 2
  • [ 3199-50-6 ]
  • [ 17357-32-3 ]
YieldReaction ConditionsOperation in experiment
65% With bromine; In 1,4-dioxane; diethyl ether; at 0 - 5℃; for 1h; To a solution of 1-(5-Bromofuran-2-yl)-ethanone (1.88 g, 10 mmol) in 12 mL dioxane/ether (1:2) with cooling at 0-5 C. and stirring was portionwise added bromine (0.52 mL, 10 mmol) over 1 h. The reaction mixture was further stirred with cooling. After TLC indicated complete bromination, the reaction mixture was diluted with ether (50 mL) and water (100 mL). The ethereal layer was separated, washed with 1 M aqueous sodium bicarbonate solution, and dried over Na2SO4. The ether extract was distilled to afford 2 in 65% yield, mp 96-97 C. (hexanes/ether, Lit. mp 98.5-99.5 C.; see Brown E., Iowa State Coll. J. Sci., 11, 221-225 (1937)). 1H NMR (CDCl3); delta 4.24 (s, 2H), 6.55 (d, J=3.6 Hz, 1H), 7.27 (d, J=3.6 Hz, 1H). 13C NMR; delta 179.0, 151.9, 129.4, 121.1, 115.0, 29.5.
  • 4
  • [ 6132-37-2 ]
  • [ 141-78-6 ]
  • [ 3199-50-6 ]
  • 5
  • [ 3199-47-1 ]
  • [ 15577-73-8 ]
  • [ 3199-50-6 ]
  • 6
  • [ 83256-79-5 ]
  • [ 623-11-0 ]
  • [ 3199-50-6 ]
  • 10
  • [ 3199-50-6 ]
  • [ 94-41-7 ]
  • 2,4-diphenyl-6-(5-bromo-2-furyl)pyrylium perchlorate [ No CAS ]
  • 14
  • 2,3-dibromo-3-<5-bromo-<2>furyl>-propionic acid ethyl ester [ No CAS ]
  • [ 3199-50-6 ]
  • 15
  • 2-bromo-3<i>t</i>-(5-bromo-[2]furyl)-acryloyl chloride [ No CAS ]
  • aq. NaOH solution (1 mol NaOH) [ No CAS ]
  • [ 3199-50-6 ]
  • 16
  • [ 3199-47-1 ]
  • [ 7732-18-5 ]
  • [ 15577-73-8 ]
  • [ 3199-50-6 ]
  • 17
  • [ 1192-62-7 ]
  • [ 3199-50-6 ]
YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide; In DMF (N,N-dimethyl-formamide); To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold water. The product was extracted with ether (200 mL, 3* times). Yield 61%, mp 92-93 C. (hexanes/ether, Lit. mp 94-95 C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931). 1H NMR (CDCl3); delta 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H). 13C NMR; delta 8185.4, 154.4, 128.2, 118.9,114.3, 25.7.
50.4% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 24h; To a solution of 1 (10 g, 90 mmol) in DMF 40 mL, NBS (19g, 108 mmol) was added by keeping the temperature at 0 C. Thereaction mixture was stirred overnight at room temperature. Upon completion,the reaction mixture was poured into ice-cold water. The mixture was dilutedwith EtOAc, and the insoluble material was filtered off through Celite. Theorganic layer of the filtrate was washed with brine, dried anhydrous magnesiumsulfate, and concentrated. The residue was chromatographed (SiO2,EtOAc/n-hexane, 1/19, v/v) to afford compound 2 (8.7 g, 45.4mmol, 50.4%). 1H NMR (500 MHz, CDCl3,delta, ppm): 2.46 (3H. s),6.49 (1H, d, J = 3.4 Hz), 7.12 (1H,d, J = 3.4 Hz). MS m/z 188 (M + H)+.
44.5% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 0.5h; Synthesis of 2-acetyl-5-bromofuran (29) 2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol). The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL x 2). The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29. Yield 1.68 g (yield rate 44.5%).
44.5% With N-Bromosuccinimide; In hexane; water; ethyl acetate; N,N-dimethyl-formamide; Synthesis of 2-acetyl-5-bromofuran (29) 2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol). The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL*2). The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29. Yield 1.68 g (yield rate 44.5%).
28% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; To a stirred solution of compound 4 (5.0 g, 45.45 mmol) and DMF (50 mL), NBS (8.8 g, 50 mmol) was added portion-wise at room temperature under stirring. The reaction mixture was allowed to stir at room temperature overnight. 50% starting material remained by TLC and LCMS. Reaction mixture was poured into cold water and the compound was extracted with diethyl ether (150 mL X 3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 5% ethyl acetate in n-hexane as an eluent to afford compound 43 (2.4 g, 28%) as a white solid.
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 5h; 2-Acetylfuran is dissolved in N,N-dimethylformamide (5 g, 1.1 mol/L), and N-bromosuccinimide (1 eq.) is added.After stirring for 5 hours at room temperature, the reaction mixture is poured into ice water and the precipitate formed is drained.1H NMR (300 MHz, CDCl3, delta in ppm): 2.47 (s, 3H); 6.49 (d, 1H, J=3.6 Hz); 7.12 (d, 1H, J=3.6 Hz).
With N-Bromosuccinimide; 90 mmol of 2-acetylfuran was dissolved in 40 mL of dimethylformamide (DMF), then 108 mmol of N-bromosuccinimide (NBS) was added at 0 C. The mixture was stirred overnight at room temperature. The mixture contained 1-(5 -bromo-2-furyl)ethanone after reaction. The reaction mixture described in Step 1 was diluted with ethyl acetate and filtered. The organic phase in the filtrate was washed with saturated salt solution and dried over anhydrous sodium sulfate, concentrated, and separated by chromatography to yield 1-(5-bromo-2-furyl)ethanone. 1H NMR (500 MHz, CDCl3, ?, ppm): 2.46 (3H. s), 6.49 (1H, d, J=3.4 Hz), 7.12 (1H, d, J=3.4 Hz). MS m/z 188 (M+H)+.

  • 18
  • C11H16BNO6S [ No CAS ]
  • [ 3199-50-6 ]
  • C17H19NO6S [ No CAS ]
  • 19
  • [ 3199-50-6 ]
  • [ 3680-93-1 ]
  • 1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-furyl)-prop-2-en-1-one [ No CAS ]
  • 20
  • [ 3199-50-6 ]
  • [ 24372-46-1 ]
  • 1-(5-bromo-2-furyl)-3-(5-dimethylamino-2-thienyl)-prop-2-en-1-one [ No CAS ]
  • 21
  • [ 3199-50-6 ]
  • [ 100-10-7 ]
  • 1-(5-bromo-2-furanyl)-3-(4-dimethylaminophenyl)-prop-2-en-1-one [ No CAS ]
  • 22
  • [ 3199-50-6 ]
  • [ 731822-24-5 ]
  • 23
  • [ 3199-50-6 ]
  • [ 731822-40-5 ]
  • 24
  • [ 3199-50-6 ]
  • [ 731822-26-7 ]
  • 25
  • [ 3199-50-6 ]
  • [ 731822-42-7 ]
  • 26
  • [ 3199-50-6 ]
  • N-methoxy-2-{5-[4-(N-methoxyamidino)phenyl]furan-2-yl}imidazo[1,2-a]pyridine-6-carboxamidine [ No CAS ]
  • 27
  • [ 3199-50-6 ]
  • [ 731822-88-1 ]
  • 28
  • [ 3199-50-6 ]
  • [ 731822-44-9 ]
  • 29
  • [ 3199-50-6 ]
  • 2-[5-(4-amidinophenyl)furan-2-yl]imidazo[1,2-a]pyridine-6-carboxamidine acetate salt [ No CAS ]
  • 30
  • [ 3199-50-6 ]
  • 2-[5-(4-amidinophenyl)furan-2-yl]-8-methylimidazo[1,2-a]pyridine-6-carboxamidine acetate salt [ No CAS ]
  • 31
  • [ 3199-50-6 ]
  • 2-[5-(4-amidinophenyl)furan-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboxamidine acetate salt [ No CAS ]
  • 33
  • [ 3199-50-6 ]
  • 1-methyl-2,4-diphenyl-6-(5-bromo-2-furyl)pyridinium perchlorate [ No CAS ]
  • 34
  • [ 3199-50-6 ]
  • [ 585-70-6 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 3199-50-6 ]

Bromides

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Related Parent Nucleus of
[ 3199-50-6 ]

Furans

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